#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/04/7220459.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7220459
loop_
_publ_author_name
'Bing, Yingying'
'Yu, Meihui'
'ming, hu'
_publ_section_title
;
 Synthesis, structures, and properties of seven transition metal
 coordination polymers based on a long semirigid dicarboxylic acid ligand
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA06012E
_journal_year                    2015
_chemical_formula_sum            'C13 H8.5 Cu0.5 N0.5 O3'
_chemical_formula_weight         251.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-03-12 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 130.336(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.434(2)
_cell_length_b                   19.805(4)
_cell_length_c                   10.6271(13)
_cell_measurement_reflns_used    422
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.6250
_cell_measurement_theta_min      4.4790
_cell_volume                     2315.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_sigmaI/netI    0.1257
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3631
_diffrn_reflns_theta_full        67.25
_diffrn_reflns_theta_max         67.25
_diffrn_reflns_theta_min         4.47
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_T_max  0.8224
_exptl_absorpt_correction_T_min  0.8097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1028
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2119
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1532
_refine_ls_R_factor_gt           0.0844
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1013P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1984
_refine_ls_wR_factor_ref         0.2529
_reflns_number_gt                1079
_reflns_number_total             2119
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra06012e2.cif
_cod_data_source_block           6b
_cod_original_cell_volume        2315.7(6)
_cod_original_sg_symbol_H-M      C2/m
_cod_original_formula_sum        'C13 H8.50 Cu0.50 N0.50 O3'
_cod_database_code               7220459
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.55524(12) 0.0000 0.65895(15) 0.0535(6) Uani 1 2 d S
O1 O 0.6516(4) 0.0693(3) 0.6544(6) 0.0642(15) Uani 1 1 d .
O2 O 0.5598(4) 0.0681(3) 0.3839(5) 0.0577(14) Uani 1 1 d .
O3 O 1.0308(5) 0.2407(4) 0.6825(6) 0.088(2) Uani 1 1 d .
N1 N 0.6793(7) 0.0000 0.9264(10) 0.053(2) Uani 1 2 d S
C1 C 0.6434(6) 0.0867(4) 0.5328(8) 0.057(2) Uani 1 1 d .
C2 C 0.7424(6) 0.1299(4) 0.5721(9) 0.057(2) Uani 1 1 d .
C3 C 0.8384(7) 0.1469(5) 0.7343(9) 0.078(3) Uani 1 1 d .
H3 H 0.8375 0.1336 0.8174 0.094 Uiso 1 1 calc R
C4 C 0.9370(7) 0.1840(5) 0.7745(9) 0.082(3) Uani 1 1 d .
H4 H 1.0008 0.1957 0.8837 0.099 Uiso 1 1 calc R
C5 C 0.9391(6) 0.2032(5) 0.6519(9) 0.065(2) Uani 1 1 d .
C6 C 0.8431(6) 0.1876(5) 0.4895(8) 0.064(2) Uani 1 1 d .
H6 H 0.8442 0.2014 0.4069 0.076 Uiso 1 1 calc R
C7 C 0.7458(6) 0.1517(4) 0.4493(8) 0.062(2) Uani 1 1 d .
H7 H 0.6812 0.1417 0.3392 0.075 Uiso 1 1 calc R
C8 C 1.1411(7) 0.2452(6) 0.8458(10) 0.069(2) Uani 1 1 d .
C9 C 1.1735(8) 0.3059(6) 0.9182(11) 0.084(3) Uani 1 1 d .
H9 H 1.1234 0.3433 0.8637 0.100 Uiso 1 1 calc R
C10 C 1.2138(9) 0.1885(6) 0.9203(12) 0.088(3) Uani 1 1 d .
H10 H 1.1889 0.1474 0.8648 0.105 Uiso 1 1 calc R
C11 C 0.6506(9) 0.0000 1.0205(12) 0.067(3) Uani 1 2 d S
H11 H 0.5683 0.0000 0.9678 0.080 Uiso 1 2 calc SR
C12 C 0.7318(13) 0.0000 1.1920(14) 0.097(5) Uani 1 2 d S
H12 H 0.7038 0.0000 1.2500 0.116 Uiso 1 2 calc SR
C13 C 0.8520(12) 0.0000 1.2727(14) 0.086(4) Uani 1 2 d S
C14 C 0.8876(10) 0.0000 1.1767(13) 0.086(4) Uani 1 2 d S
H14 H 0.9695 0.0000 1.2274 0.103 Uiso 1 2 calc SR
C15 C 0.7984(9) 0.0000 1.0042(12) 0.072(4) Uani 1 2 d S
H15 H 0.8226 0.0000 0.9416 0.086 Uiso 1 2 calc SR
C16 C 0.9429(11) 0.0000 1.4600(15) 0.140(7) Uani 1 2 d S
H16 H 0.9147 0.0000 1.5178 0.168 Uiso 1 2 calc SR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 Cu1 O2 87.4(3) 5_656 2_656
O2 Cu1 O1 168.66(19) 5_656 .
O2 Cu1 O1 91.2(2) 2_656 .
O2 Cu1 O1 91.2(2) 5_656 6
O2 Cu1 O1 168.66(19) 2_656 6
O1 Cu1 O1 87.9(3) . 6
O2 Cu1 N1 99.3(2) 5_656 .
O2 Cu1 N1 99.3(2) 2_656 .
O1 Cu1 N1 92.0(2) . .
O1 Cu1 N1 92.0(2) 6 .
O2 Cu1 Cu1 89.04(13) 5_656 5_656
O2 Cu1 Cu1 89.04(13) 2_656 5_656
O1 Cu1 Cu1 79.67(15) . 5_656
O1 Cu1 Cu1 79.67(15) 6 5_656
N1 Cu1 Cu1 168.4(2) . 5_656
C1 O1 Cu1 127.7(5) . .
C1 O2 Cu1 118.0(5) . 5_656
C5 O3 C8 118.6(6) . .
C11 N1 C15 116.3(9) . .
C11 N1 Cu1 127.0(7) . .
C15 N1 Cu1 116.7(7) . .
O1 C1 O2 125.2(7) . .
O1 C1 C2 115.8(6) . .
O2 C1 C2 119.0(6) . .
C3 C2 C7 118.3(7) . .
C3 C2 C1 119.9(7) . .
C7 C2 C1 121.7(6) . .
C2 C3 C4 120.5(7) . .
C2 C3 H3 119.7 . .
C4 C3 H3 119.7 . .
C5 C4 C3 119.8(7) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
O3 C5 C4 122.6(6) . .
O3 C5 C6 117.2(7) . .
C4 C5 C6 120.1(7) . .
C7 C6 C5 120.3(7) . .
C7 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C6 C7 C2 120.9(6) . .
C6 C7 H7 119.6 . .
C2 C7 H7 119.6 . .
C9 C8 C10 123.1(8) . .
C9 C8 O3 117.5(9) . .
C10 C8 O3 119.2(9) . .
C8 C9 C10 118.0(10) . 7_757
C8 C9 H9 121.0 . .
C10 C9 H9 121.0 7_757 .
C8 C10 C9 118.9(9) . 7_757
C8 C10 H10 120.6 . .
C9 C10 H10 120.6 7_757 .
N1 C11 C12 126.0(11) . .
N1 C11 H11 117.0 . .
C12 C11 H11 117.0 . .
C13 C12 C11 118.7(12) . .
C13 C12 H12 120.7 . .
C11 C12 H12 120.7 . .
C12 C13 C14 117.5(10) . .
C12 C13 C16 119.9(12) . .
C14 C13 C16 122.6(12) . .
C15 C14 C13 119.4(11) . .
C15 C14 H14 120.3 . .
C13 C14 H14 120.3 . .
N1 C15 C14 122.1(11) . .
N1 C15 H15 118.9 . .
C14 C15 H15 118.9 . .
C16 C16 C13 121.4(18) 5_758 .
C16 C16 H16 119.3 5_758 .
C13 C16 H16 119.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O2 1.950(5) 5_656
Cu1 O2 1.950(5) 2_656
Cu1 O1 1.977(5) .
Cu1 O1 1.977(5) 6
Cu1 N1 2.167(8) .
Cu1 Cu1 2.642(3) 5_656
O1 C1 1.267(8) .
O2 C1 1.274(8) .
O2 Cu1 1.950(5) 5_656
O3 C5 1.359(9) .
O3 C8 1.406(9) .
N1 C11 1.306(13) .
N1 C15 1.342(12) .
C1 C2 1.476(10) .
C2 C3 1.384(10) .
C2 C7 1.405(10) .
C3 C4 1.400(10) .
C3 H3 0.9300 .
C4 C5 1.377(10) .
C4 H4 0.9300 .
C5 C6 1.378(9) .
C6 C7 1.371(9) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C9 1.339(13) .
C8 C10 1.383(12) .
C9 C10 1.410(11) 7_757
C9 H9 0.9300 .
C10 C9 1.410(11) 7_757
C10 H10 0.9300 .
C11 C12 1.389(14) .
C11 H11 0.9300 .
C12 C13 1.348(17) .
C12 H12 0.9300 .
C13 C14 1.408(16) .
C13 C16 1.517(15) .
C14 C15 1.401(13) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C16 1.28(3) 5_758
C16 H16 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O2 Cu1 O1 C1 -11.3(15) 5_656 .
O2 Cu1 O1 C1 -94.2(7) 2_656 .
O1 Cu1 O1 C1 74.5(7) 6 .
N1 Cu1 O1 C1 166.4(6) . .
Cu1 Cu1 O1 C1 -5.4(6) 5_656 .
O2 Cu1 N1 C11 -44.46(16) 5_656 .
O2 Cu1 N1 C11 44.46(16) 2_656 .
O1 Cu1 N1 C11 136.00(17) . .
O1 Cu1 N1 C11 -136.00(17) 6 .
Cu1 Cu1 N1 C11 180.000(8) 5_656 .
O2 Cu1 N1 C15 135.54(16) 5_656 .
O2 Cu1 N1 C15 -135.54(16) 2_656 .
O1 Cu1 N1 C15 -44.00(17) . .
O1 Cu1 N1 C15 44.00(17) 6 .
Cu1 Cu1 N1 C15 0.000(7) 5_656 .
Cu1 O1 C1 O2 9.4(12) . .
Cu1 O1 C1 C2 -168.3(5) . .
Cu1 O2 C1 O1 -7.0(11) 5_656 .
Cu1 O2 C1 C2 170.6(5) 5_656 .
O1 C1 C2 C3 2.3(12) . .
O2 C1 C2 C3 -175.6(8) . .
O1 C1 C2 C7 178.8(7) . .
O2 C1 C2 C7 0.9(12) . .
C7 C2 C3 C4 -1.0(14) . .
C1 C2 C3 C4 175.6(8) . .
C2 C3 C4 C5 -0.7(15) . .
C8 O3 C5 C4 17.0(14) . .
C8 O3 C5 C6 -166.3(8) . .
C3 C4 C5 O3 178.4(8) . .
C3 C4 C5 C6 1.8(15) . .
O3 C5 C6 C7 -178.0(8) . .
C4 C5 C6 C7 -1.2(14) . .
C5 C6 C7 C2 -0.5(13) . .
C3 C2 C7 C6 1.6(13) . .
C1 C2 C7 C6 -175.0(8) . .
C5 O3 C8 C9 -115.1(10) . .
C5 O3 C8 C10 68.6(11) . .
C10 C8 C9 C10 -1.5(16) . 7_757
O3 C8 C9 C10 -177.6(7) . 7_757
C9 C8 C10 C9 1.6(17) . 7_757
O3 C8 C10 C9 177.6(7) . 7_757
C15 N1 C11 C12 0.000(10) . .
Cu1 N1 C11 C12 180.000(5) . .
N1 C11 C12 C13 0.000(7) . .
C11 C12 C13 C14 0.000(10) . .
C11 C12 C13 C16 180.000(9) . .
C12 C13 C14 C15 0.000(10) . .
C16 C13 C14 C15 180.000(10) . .
C11 N1 C15 C14 0.000(5) . .
Cu1 N1 C15 C14 180.000(7) . .
C13 C14 C15 N1 0.000(6) . .
C12 C13 C16 C16 180.000(14) . 5_758
C14 C13 C16 C16 0.000(4) . 5_758
